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Pyrrolidine → [8-Methyl-2-(pyrrolidin-1-yl)quinolin-3-yl]methanol

HRID 1627506
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HRID 1627506 반응식
Cl[C:2]1[C:11]([CH2:12][OH:13])=[CH:10][C:9]2[C:4](=[C:5]([CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>CCOC(C)=O>[CH3:14][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[C:11]([CH2:12][OH:13])=[CH:10]2
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참가 물질

4

반응물 2

HCID 31268PyrrolidineHCID 865104(2-Chloro-8-methylquinolin-3-yl)methanol

생성물 1

HCID 66777627[8-Methyl-2-(pyrrolidin-1-yl)quinolin-3-yl]methanol수율 88%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

(2-Chloro-8-methylquinolin-3-yl)methanol (200 mg, 0.97 mmol) and pyrrolidine (2 mL) were stirred in a sealed tube at 100° C. for 4 h. After cooling, the solution was diluted with EtOAc and washed with water and brine. The organic layer was dried (MgSO4), filtered and the solvent was removed in vacuo. Purification by column chromatography on silica, eluting with 20% EtOAc in isohexane, gave the title compound (206 mg, 88%). δH (CDCl3) 7.86 (1H, s), 7.46 (1H, d, J=8.01 Hz), 7.40 (1H, d, J=7.04 Hz), 7.13 (1H, t, J=7.50 Hz), 4.85 (2H, s), 3.72 (4H, t, J=6.36 Hz), 2.65 (3H, s), 2.12 (1H, s), 2.03-1.96 (4H, m).

후처리

  1. temperatureAfter cooling
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customPurification by column chromatography on silica
  7. washeluting with 20% EtOAc in isohexane

출처 및 근거

ORD 기록
ord-bab2f63a6668458aa7844ae7a89d2f65
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785628B2

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